5.09 The Cell:
FLASHBACKS TO A DARK TIME IN DAMON’S LIFE — Stefan (Paul Wesley) continues to offer Katherine (Nina Dobrev) his support while trying to mask his own pain, until Caroline (Candice Accola) shows up with an unusual form of therapy. After trying to make amends with Caroline, Elena (Nina Dobrev) grows so concerned about Damon (Ian Somerhalder) that she turns to Aaron (guest star Shaun Sipos) for help. Later, when Damon tells Elena about a terrible ordeal in his past that he has kept secret for decades, she shares the disturbing information she just learned about her own family. Finally, Aaron decides on a desperate course of action after a conversation with Dr. Wes (guest star Rick Cosnett). Chris Grismer directed the episode written by Melinda Hsu Taylor (#509).
5.10 Fifty Shades Of Grayson
DAMON’S PAST RETURNS TO HAUNT HIM — Damon (Ian Somerhalder) realizes Elena (Nina Dobrev) is in danger and enlists Stefan’s (Paul Wesley) help to find her. The brothers pay a visit to Aaron (guest star Shaun Sipos), and Damon shocks Stefan by revealing his first-hand knowledge of Aaron’s family. In an attempt to stop Damon, Dr. Wes (guest star Rick Cosnett) unleashes his secret weapon, forcing Damon to deal with a part of his past he thought was gone forever, as well as the consequences of his decades-long plan for revenge. Meanwhile, Elena is horrified by Dr. Wes’ confessions about the dark history of Whitmore College and his own ultimate goal. Finally, a frantic Katherine (Nina Dobrev) turns to Matt (Zach Roerig) for help, until she realizes that Nadia (guest star Olga Fonda) may be the one who can solve her problem. Kellie Cyrus directed the episode written by Caroline Dries (#510).